Ethanamine, 2,2,2-trifluoro- → 6-chloro-4-(4-bromophenyl)-4-hydroxy-3-(2,2,2-trifluoroethyl)-3,4-dihydroquinazolin-2(1H)-one

HRID 19694

Reaktionsgleichung

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](N2C=CN=C2)=[O:10])=[C:4]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=2)[CH:3]=1.[F:25][C:26]([F:30])([F:29])[CH2:27][NH2:28]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[NH:8][C:9](=[O:10])[N:28]([CH2:27][C:26]([F:30])([F:29])[F:25])[C:16]2([C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=1)[OH:24]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a solution of N-[4-chloro-2-(4-bromobenzoyl)phenyl]-1H-imidazole-1-carboxamide (4.0 g, 9.9 mmol) in THF (20 mL) was added 2,2,2-trifluoroethylamine (1.1 g, 10.9 mmol). The reaction was heated to 50° C. After 19 h at 50° C., the reaction was cooled to ambient temperature and concentrated in vacuo. The light yellow foam was partitioned between n-butyl chloride (15 mL) and aqueous 10% citric acid (15 mL) with vigorous stirring. The resulting precipitate was collected by vacuum filtration to give 6-chloro-4-(4-bromophenyl)-4-hydroxy-3-(2,2,2-trifluoroethyl)-3,4-dihydroquinazolin-2(1H)-one as a white solid. 1H NMR (CDCl3, 500 MHz) δ 7.98 (s, 1H); 7.50 (br d, 2H, J=8.79 Hz); 7.34 (br d, 2H, J=8.79 Hz); 7.22 (m, 2H); 6.97 (dd, J=1.46 and 7.57 Hz, 1H); 4.35 (dq, 1H, J=8.78 and 16 Hz); 3.53 (dq, 1H, J=8.55 and 17 Hz); 3.22 (s, 1H). MS (Electrospray): m/z M+Na, Br=79, 457.0

Aufarbeitung

temperaturethe reaction was cooled to ambient temperature
concentrationconcentrated in vacuo
customThe light yellow foam was partitioned between n-butyl chloride (15 mL) and aqueous 10% citric acid (15 mL) with vigorous stirring
filtrationThe resulting precipitate was collected by vacuum filtration

Quellen und Nachweise

ORD-Eintrag: ord-d9c1d5bcf40444489680aaafc635997e
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07745452B2

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